The series was noted for its micromanagement, where the player had to do the job of the team manager and much of that of the chairman, from player training up to bank balance management. Other well-known features were to bung an opposing team for preferential market treatment, rig or betting on the outcome of the players' team matches. Interviews after the match where some answers were printed with different interpretations on the next days' newspaper (the player could reply a question about the game with "It was a game of two halves", and "He amazed us after the game by giving us an insight into the rules of football" would be printed on the newspapers).

In all three games, the game always kept the same visual style: the main screen is a bird's eye view of the stadium facility (where clicking on the grass brings the squad selection screen or in the stands for the stadium builder) and all screens are presented like the player was inside an office (TCM 2004 used a similar interface option). To increase the feeling of "being there", tables are accessed via teletext, news from a newspaper and fixtures are available by clicking on a sheet attached on a clipboard.

While improving with each game, most features were the same from the start of the series. The game compared favourably in all areas but AI against its leading competitor, Championship Manager. While similar in name, it has no relations with Ultimate Soccer.

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The original version of the game provided the English league system from the FA Premier League down to the Football Conference. It was distributed as shareware, with a fully functional demo in which the player could only select then Second Division side Brighton and Hove Albion. The game allowed to watch games in top-down view, buy and sell players, manage the team, upgrade the stadium and manage commercial interests such as advertising and merchandise.[1]

The game received a rating of 83% from Amiga computing.[1] The review stating the game's graphic approach and coverage of business issues made it stand out in the crowded football management simulation market.[1] The graphics the game used for actual matches however were considered poor.[1]

In 1996, a data disk for the Amiga version was released, covering the 1995-1996 season.

The second version of the game, USM 2 ran in protected mode, featured a more polished interface (plus teams and players of the 1996-1997 season and also the French and German leagues (although in the last the final name of the players had a letter swapped to avoid legal problems regarding licensing) which could be accessed with different executables. In Germany, a localized version of the game was released under the name "DSF Fussball Manager", DSF being a well-known German TV sports channel.

This version of the game was updated to run natively on Windows 95 and Windows 98 and included teams, players and statistics from the 1997-1998 season. The number of leagues increased to five, as both Italian and Scottish championships were added. Transfers required often a week or more of fax exchange between clubs and with the player agent, making the game more realistic than most other games in this aspect, which only required the player to bid for the player and agree wage and length, adding him instantaneously to the team. USM 98 was released as "DSF Fussball Manager 98" for the German market.

An update disk (also available as a stand-alone) named Ultimate Soccer Manager 98-99 Season Update Add-on was sold shortly after the game came out with statistics for the 1998-1999 season, which also included both Spanish and Dutch top two divisions, increasing the number to seven playable leagues. While several bugs were ironed (such as a giving one of the assistants a wage of £99'999'999, and then after offering him a new contract he would start paying the club around £13M weekly, a glitch that carried from USM 2), it became clear that many teams would allow their superstar players to end contract, allowing the player to pick them for free (although with a large salary). Similarly, you could loan a big-name player worth millions and then use him as a makeweight in transfer deals.

As the official pre-game editor included in the game was poor, some USM users produced enhanced pre-game editors. USM Data Editor (USMDE or UDE), of which the official web site was included in the USM Online web site (usm.footymanager.net), was called as the best editor. USMDE includes various features for USM98 editing, e.g., creating players, editing hidden stats, add-on file support for easy data update by USM fans, beta-released save game editing.

There was a planned 2000 version of the game, which was developed. However, the game was thought to be scrapped after Sierra UK became impatient with the game's development progress. The game was set to have an "all-new 3D match engine with advanced Artificial Intelligence".[2] It is also believed that the coding was rewritten.

After posting on a Facebook group dedicated to the game Ande Pearson and Dane Smallbone decided to work together to update all player and team data for the 2012/2013 season. The data update took months of painstaking data collection and in game testing but finally completed it. The German league was the only league not updated due to the large structure change to the leagues since the game was released. The data file is available to download from the Facebook group titled 'Ultimate Soccer Manager Update,

The game sometimes crashes when is played for a large number of in-game seasons. The problems with savegames include: no possibility of viewing detailed info on some players (the game quits after double-clicking on player's name), wrong statistics about some players (ex. incorrect information about scored goals etc.) or even an unexpected exit of the game after viewing post-match statistics. The best way to cope with these problems is to make a lot of savegames, for ex. every in-game month. The game does not run properly on Windows XP. But it runs smoothly on Windows 98, so you can use a free software like Microsoft Virtual Machine with Windows 98 on Windows XP to run the game.